ZA200201393B - Compound safety glass and PVB foil for the production thereof. - Google Patents
Compound safety glass and PVB foil for the production thereof. Download PDFInfo
- Publication number
- ZA200201393B ZA200201393B ZA200201393A ZA200201393A ZA200201393B ZA 200201393 B ZA200201393 B ZA 200201393B ZA 200201393 A ZA200201393 A ZA 200201393A ZA 200201393 A ZA200201393 A ZA 200201393A ZA 200201393 B ZA200201393 B ZA 200201393B
- Authority
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- South Africa
- Prior art keywords
- weight
- plasticizer
- general formula
- glycol
- safety glass
- Prior art date
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- 239000005336 safety glass Substances 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 title 1
- 239000011888 foil Substances 0.000 title 1
- 239000004014 plasticizer Substances 0.000 claims description 43
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 claims description 35
- 238000009413 insulation Methods 0.000 claims description 31
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 31
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 27
- 239000011521 glass Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 15
- -1 polybutylene Polymers 0.000 claims description 15
- 229920001223 polyethylene glycol Polymers 0.000 claims description 13
- 239000002202 Polyethylene glycol Substances 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 8
- 229920001400 block copolymer Polymers 0.000 claims description 7
- HHECSPXBQJHZAF-UHFFFAOYSA-N dihexyl hexanedioate Chemical compound CCCCCCOC(=O)CCCCC(=O)OCCCCCC HHECSPXBQJHZAF-UHFFFAOYSA-N 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- GCDUWJFWXVRGSM-UHFFFAOYSA-N 2-[2-(2-heptanoyloxyethoxy)ethoxy]ethyl heptanoate Chemical compound CCCCCCC(=O)OCCOCCOCCOC(=O)CCCCCC GCDUWJFWXVRGSM-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000002334 glycols Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229920001748 polybutylene Polymers 0.000 claims description 3
- 159000000032 aromatic acids Chemical class 0.000 claims description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 18
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 239000004372 Polyvinyl alcohol Substances 0.000 claims 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 claims 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims 1
- 125000001033 ether group Chemical group 0.000 claims 1
- 229940116351 sebacate Drugs 0.000 claims 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 claims 1
- 239000005340 laminated glass Substances 0.000 description 11
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 6
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- UZVAZDQMPUOHKP-UHFFFAOYSA-N 2-(7-methyloctyl)phenol Chemical compound CC(C)CCCCCCC1=CC=CC=C1O UZVAZDQMPUOHKP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920002266 Pluriol® Polymers 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical class CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- 241000640882 Condea Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 239000002313 adhesive film Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical class OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- GWQRPOCMBMQBTK-UHFFFAOYSA-N 2-[2-(2-ethylhexanoyloxy)ethoxy]ethyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OCCOCCOC(=O)C(CC)CCCC GWQRPOCMBMQBTK-UHFFFAOYSA-N 0.000 description 1
- JEYLQCXBYFQJRO-UHFFFAOYSA-N 2-[2-[2-(2-ethylbutanoyloxy)ethoxy]ethoxy]ethyl 2-ethylbutanoate Chemical compound CCC(CC)C(=O)OCCOCCOCCOC(=O)C(CC)CC JEYLQCXBYFQJRO-UHFFFAOYSA-N 0.000 description 1
- SSKNCQWPZQCABD-UHFFFAOYSA-N 2-[2-[2-(2-heptanoyloxyethoxy)ethoxy]ethoxy]ethyl heptanoate Chemical compound CCCCCCC(=O)OCCOCCOCCOCCOC(=O)CCCCCC SSKNCQWPZQCABD-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- GPZYYYGYCRFPBU-UHFFFAOYSA-N 6-Hydroxyflavone Chemical compound C=1C(=O)C2=CC(O)=CC=C2OC=1C1=CC=CC=C1 GPZYYYGYCRFPBU-UHFFFAOYSA-N 0.000 description 1
- OIUGWVWLEGLAGH-UHFFFAOYSA-N 6-nonoxy-6-oxohexanoic acid Chemical class CCCCCCCCCOC(=O)CCCCC(O)=O OIUGWVWLEGLAGH-UHFFFAOYSA-N 0.000 description 1
- SXKCDRRSQHPBOI-UHFFFAOYSA-N 6-o-cyclohexyl 1-o-hexyl hexanedioate Chemical compound CCCCCCOC(=O)CCCCC(=O)OC1CCCCC1 SXKCDRRSQHPBOI-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000004435 Oxo alcohol Substances 0.000 description 1
- 206010041662 Splinter Diseases 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- FRQDZJMEHSJOPU-UHFFFAOYSA-N Triethylene glycol bis(2-ethylhexanoate) Chemical compound CCCCC(CC)C(=O)OCCOCCOCCOC(=O)C(CC)CCCC FRQDZJMEHSJOPU-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000011354 acetal resin Substances 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- OJXOOFXUHZAXLO-UHFFFAOYSA-M magnesium;1-bromo-3-methanidylbenzene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C1=CC=CC(Br)=C1 OJXOOFXUHZAXLO-UHFFFAOYSA-M 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001290 polyvinyl ester Polymers 0.000 description 1
- 230000003763 resistance to breakage Effects 0.000 description 1
- 239000005368 silicate glass Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- PIAOXUVIBAKVSP-UHFFFAOYSA-N γ-hydroxybutyraldehyde Chemical compound OCCCC=O PIAOXUVIBAKVSP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
- B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
- B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
- B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
- B32B17/10605—Type of plasticiser
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
- B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
- B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
- B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
- B32B17/10761—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer containing vinyl acetal
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L29/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical; Compositions of hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Compositions of derivatives of such polymers
- C08L29/14—Homopolymers or copolymers of acetals or ketals obtained by polymerisation of unsaturated acetals or ketals or by after-treatment of polymers of unsaturated alcohols
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2307/00—Properties of the layers or laminate
- B32B2307/10—Properties of the layers or laminate having particular acoustical properties
- B32B2307/102—Insulating
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31627—Next to aldehyde or ketone condensation product
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31627—Next to aldehyde or ketone condensation product
- Y10T428/3163—Next to acetal of polymerized unsaturated alcohol [e.g., formal butyral, etc.]
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Joining Of Glass To Other Materials (AREA)
- Laminated Bodies (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
[ ’ o WO 01/19747 -1 - PCT/DEO0/02743
The invention relates to laminated safety glass with improved acoustic properties, and also to a PVB film for producing the same. Laminated safety glass is generally composed of two panes of glass and of an adhesive film bonding the panes. The vast majority of adhesive films used are films made from plasticized, partially acetalized polyvinyl alcohols, in particular from polyvinyl butyral (PVB). Examples of use of the abovementioned laminated safety glass are windscreens in the motor vehicle sector, and also glazing in the construction sector.
The plasticizers mainly used in industry for PVB are aliphatic diesters of tri- or tetraethylene glycol.
These include 3GH, 3G7, 3G8, and also 4G7, where the prefixed figure indicates the number n in the repeat unit H- (O-CH,-CH,),—OH of the oligoethylene glycol fraction and H indicates 2-ethylbutyrate, 7 indicates n-heptanoate and 8 indicates 2-ethylhexanoate. Examples of other known plasticizers for polyvinyl butyral are dialkyl adipates with aliphatic or, respectively, cycloaliphatic ester components, dialkyl sebacates, : triorganophosphates, triorganophosphites and phthalate plasticizers, such as benzyl butyl phthalate.
Compared with monolithic panes of glass with the same overall thickness, laminated safety glass has higher sound insulation. This is attributable to the fact that the elasticity of the PVB film reduces the mechanical coupling between the individual panes, and thus hinders the transfer of vibration from the side of the pane facing the sound source to the opposite side of the pane. ) REPLACEMENT SHEET (RULE 26)
~ 26-09-200211 op 00ass won DE0002743
The insulation efficiency of glazing can be determined as a function of the frequency to DIN 52210 or
DIN EN ISO 717, and is expressed by the sound insulation value Ry, which is a weighted average over the frequency range from 100 to 3150 Hz relevant for the acoustics of buildings. A higher value Ry; here represents better sound insulation by the glazing. For example, a pane of conventional laminated glass with the structure 3 mm of glass/0.38 mm of PVB film/3 mm of glass can achieve a R, of 33 dB, whereas 32 dB is the value measured for a monolithic pane of thickness 6 mm.
However, the insulation performance of known laminated safety glass is inadequate for many applications. When the sound insulation provided by laminated safety glass of the prior art, with a conventional PVB film as intermediate layer, is measured at room temperature the insulation rises steadily and approximately linearly within a wide range with increasing frequency, but a marked drop in insulation (relative minimum in insulation, coincidence drop) can be seen in particular in the frequency range from about 1000 to 3500 Hz. The position of this coincidence drop depends on the thickness of the glasses used. If each of the panes used has a thickness of 4 mm the coincidence drop is approximately in the range from 1 250 to 2 500 Hz, and if thinner panes are used the insulation drop shifts to higher frequencies, while the range is shifted toward lower frequencies if thicker panes are used. The term coincidence frequency is used below for the frequency at which the insulation curve passes through the relative minimum in the range of the coincidence drop.
Prior art
Proposals have previously been made for improving the sound insulation performance of laminated safety glass.
US 5,773,102 (= EP 0 763 420 Al) and JP 07-097241 A
AMENDED SHEET ox 26-09-2001; oy 0040s woun DE0002743 disclose laminated safety glass in which a specific acoustic film is used, besides a standard PVB film, to improve acoustic properties.
DE 197 05 586 Cl and EP 0 844 075 Al likewise propose a thermoplastic intermediate layer itself having more than one layer, for a sound-insulating laminated pane of glass for motor vehicles. The laminate is composed of a viscoelastic acrylic polymer film, each side of which has been bonded via a polyethylene terephthalate film of from 0.01 to 0.1 mm thickness and a thermoplastic adhesive polyvinyl butyral film to two panes of silicate glass.
However, intermediate layers of this type which themselves have more than one layer involve complications in production, and frequently also in further processing.
Finally, DE 24 61 775 Al discloses laminated safety glass in which, although the addition of very large amounts of standard plasticizer, in this case Flexol, achieves improved sound insulation, the amount of plasticizer used leads to increased tack, and the film therefore has limited capability for further processing using conventional systems.
JP 11-106595 A relates to a PVB batch containing from 20 to 80% by weight of an ether-ester plasticizer per 100 parts by weight of polyvinyl butyral resin. The plasticizer in turn contains from 20 to 60% by weight of triethylene glycol bis(2—ethylhexancate) (3G8) and 40-80% by weight of a disubstituted polyethylene glycol. The object on which this citation was based was to achieve a PVB batch having good low-temperature stability and good mechanical properties of the
AMENDED SHEET o 26-09-2001; oz 00405 woun DE0002743 laminated safety glass. There is no reference in this text to improved sound insulation.
Us 5,332,774 A discloses a film made of partly acetalized polyvinyl alcohols and containing plasticizer, the film being suitable for the production of laminated safety glass. The polyvinyl alcohols are acetalized using 4-hydroxybutanal. The polyvinyl acetal resins prepared in this way, however, can according to this citation not be plasticized with conventional plasticizers. For this reason, special plasticizers are used, including certain polyalkylene glycols. This text gives no indication of an improvement in the sound insulation performance.
EP O 041 229 A discloses the use of poly(propylene oxide) derivatives as plasticizers for PVB. This document does not give rise to any indications whatsoever of particular mixing proportions with standard plasticizers or of the acoustic efficacy of such plasticizer mixtures.
Object
It is therefore an object of the present invention to provide, for laminated glass, an intermediate film which if possible has one layer and which is based on
PVB, and which can give the laminated glass produced from the same improved sound insulation at room temperature, without any substantial alteration in ease of processing. A further object of the invention is to provide laminated glass having an intermediate layer based on PVB and providing improved sound insulation at room temperature.
The invention achieves this object by means of laminated safety glass according to claim 1, preferably
AMENDED SHEET
. 26-09-2001; 0 0049s Hoon DE0002743 combined with one or more of the features of the subclaims, and, respectively, by means of a sound insulating film according to claim 7, and the use of certain polyalkylene glycols according to claim 8.
At the heart of the present invention is the use of a polyalkylene glycol of the formula HO-(R-0),-H or certain derivatives of the same as a plasticizer, in addition to at least one first plasticizer known per se, 1n a PVB film.
Compared with conventional plasticizers, polyalkylene glycol or certain derivatives of the same used as coplasticizer in a PVB film bring about a marked improvement in sound insulation in laminated glass produced with a film of this type. In particular, the otherwise pronounced fall-off of sound insulation in the coincidence region is significantly less pronounced. Compared with a standard film composition, the proportion of polyvinyl butyral and/or of the standard plasticizer used in each case in the PVB film can be reduced and replaced by a polyalkylene glycol or a derivative of the same. The general embodiment of the invention is characterized by the fact that the polyalkylene glycol or, respectively, a derivative of the same, mixed with one or more conventional plasticizers, plasticizes the PVB resin.
In the general embodiment of the invention the total of the plasticizing components (polyalkylene glycol + conventional plasticizer) makes up from 20 to 50% by weight of the film. In its preferred embodiment the total plasticizer content is from 25 to 40% by weight and in the most preferred embodiment is from 30 to 35% by weight. The proportion of the polyalkylene glycol of the invention in the film here amounts to more than 5% by weight and to more than 10% by weight in the
AMENDED SHE:T
- 26-09-2001; o; 0020s Hon DE0002743 preferred case, in each case based on the total composition of the film.
For the purposes of the invention, polyalkylene glycols are those which have an average degree of polymerization DP of 6 or higher, but where this degree is not so high that combination with the other components of the film gives unacceptable haze in the laminated glass. Haze values which should be regarded as unacceptable when measured to ASTM D1003-6 are those above 3% haze or, respectively, )L deviations between greater than 3 found in comparative measurements of the duplex glass laminated with PVB film and duplex glass with no PVB film and taking L (iaminate)—L (duplex glass) = JL in accordance with DIN 5033. The haze values are preferably below 1.5%, in particular below 1% haze for a film thickness of 0.76 mm.
For the purposes of the invention, the specific polyalkylene glycols may be poly(ethylene oxides), including block copolymers of the type HO-(CHy;—-CHy-O)n- (CH,-CH (CH3) -0) n—H, poly (propylene oxides) or poly- (butylene oxides), or else derivatives of the same, but poly (propylene oxides) are not preferred, since their effectiveness is low. The non-derivatized polyalkylene glycols of the invention should have an average degree of polymerization - referred to below as DP - of at least 6. Examples here are Pluriol® E 600 from BASF with an average degree of polymerization DP of 13.6 and
Pluriol® P 2000 from BASF with an average degree of polymerization DP of 15.5.
For the purposes of the invention, derivatives of polyalkylene glycols are those in which the hydrogen of one of the two terminal hydroxyl groups of the polyalkylene glycol has been replaced by an organic radical. Possible examples here are ethoxylated fatty
AMENDED SHEET
26-09-2001 op 0s0s won DE0002743 - 7 = alcohols, ethoxylated fatty acids, such as the polyethylene glycol ester of oleic acid, or monoethers of polyalkylene glycol with monohydric aliphatic alcohols, such as methanol or ethanol. Other examples are Marlonhen® NP 6 from Condea whose structure has a polyethylene glycol fraction with a DP of 6 and an isononylphenol fraction on one of the two hydroxyl- terminated ends, and also Marlipal® 0 13/100 from
Condea, whose structure has a polyethylene glycol fraction with a DP of 10 and a Ci;3 oxo alcohol. In these monoderivatives of polyalkylene glycols, the DP of the polyalkylene glycol fraction must be at least 2. The upper DP limit is given by the compatibility with the other components of the film.
The resins used in the novel film are partially acetalized polyvinyl alcohols known per se, in particular polyvinyl butyral. The partially acetalized polyvinyl alcohols are prepared in a known manner by acetalizing hydrolyzed polyvinyl esters. Examples of aldehydes which may be used are formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde and the like, preferably butyraldehyde. The preferred polyvinyl butyral resin contains from 10 to 25% by weight, preferably from 17 to 23% by weight and particularly preferably from 19 to 22% by weight, of vinyl alcohol radicals. The polyvinyl butyral may also, if desired, contain from 0 to 20% by weight, preferably from 0.5 to 2.5% by weight, of acetate radicals. Wherever the term polyvinyl butyral or PVB is used in this application it generally also includes the other partially acetalized polyvinyl alcohols.
Besides the above-described polyalkylene glycols according to the invention, at least one further plasticizer is used. This is preferably a standard plasticizer selected from the group consisting of
AMENDED SHEET
- 26-09-2001; og 0049s s0.a | DE0002743 ~- 8 - - esters of polybasic aliphatic or aromatic acids, e.g. dialkyl adipates such as dihexyl adipate, dioctyl adipate, hexyl cyclohexyl adipate, mixtures of hepty and nonyl adipates, diisononyl adipate, heotvl nonvl adivate. and also esters of adipic acid with cycloaliphatic ester alcohols, dialkyl sebacates such as dibutyl sebacate, and phthalates such as butyl benzyl phthalate; - esters of polyhydric aliphatic or aromatic alcohols or oligoether glycols having not more than four ethylene glycol units with one or more unbranched or branched aliphatic or aromatic substituents, e.g. esters of di-, tri- or tetraglycols with linear or branched aliphatic or cycloaliphatic carboxylic acids; Diethylene glycol bis (2-ethylhexanoate), triethylene glycol bis (2-ethylhexanoate), tri- ethylene glycol bis (2-ethylbutanoate), tetraethylene glycol bis-n-heptanoate, triethylene glycol bis-n- heptanoate, and triethylene glycol Dbis-n-hexanoate can serve as examples of the latter group.
Particularly preferred standard plasticizers are di-n-hexyl adipate (DHA) and triethylene glycol bis- n-heptanoate (3G7).
To produce the novel PVB film with improved sound insulation, the liquid, paste or solid polyalkylene glycol component is mixed with the standard plasticizer, giving either a homogeneous solution of the polyalkylene glycol component in the plasticizer or, if the polyalkylene glycol component and plasticizer are incompatible, a dispersion. The mixture made from plasticizer and polyalkylene glycol component is then ©processed together with the pulverulent polyvinyl butyral, while supplying heat and mechanical work, to give a homogeneous film mass, and this material is preferably extruded through a flat-film die
AMENDED SHEET
- 26-09-20011 0 00ass won DE0002743 — 8a —- to give a web of film. Further constituents which may, if desired, be present in the film are dyes, light stabilizers, stabilizers, processing aids, water, and also adhesion regulators.
The water content of the films is preferably set at from 0.15 to 0.8% by weight, more preferably at from 0.4 to 0.7% by weight.
Besides the improved insulation properties, the novel laminated safety (glass (LSG) has the properties featured by LSG, such as resistance to breakage, splinter retention and transparency. For example, adhesion tests on the glass using a pummel test give values of 8-10 for the fire side and 7 for the tin side of the glass.
Methods of working the invention, and also comparative example
Example 1 22 parts by weight of triethylene glycol Dbis- n-heptanocate (3G7) as standard plasticizer, together with 11 parts by weight of Pluriol® 600, an unsubstituted poly(ethylene glycol) with an average molar mass of 600 [g/mol] or an average degree of polymerization DP of 13.6, and also 0.15 part by weight of Tinuvin® P UV absorber (manufacturer: Ciba) were added to 67 parts by weight of a polyvinyl butyral resin with a vinyl alcohol radical content (OH group content calculated as vinyl alcohol content) of 20.5% by weight and a vinyl acetate radical content of 0.7% by weight. The mixture was extruded at a melt
AMENDED SHEET temperature of about 200°C in a twin-screw extruder with a flat-film die to give a transparent film of thickness 0.76 mm.
The PVB film and each of two panes of glass of dimensicns 1480 x 1230 x 4 mm then undervrant a lamination process, by simultaneous heating and compression in an autoclave, to give panes of laminated glass. The sound insulation value Ry of these panes was determined to DIN EN ISO 717 across the frequency band from 50 Hz to 5000 Hz at frequency intervals of one third of an octave. The temperature of the test specimen and of the test room was 21°C. Results of these measurements are shown in diagram 1 in the form of an insulation curve, in which higher values measured at a particular frequency signify better insulation.
Comparative example (example 2)
The insulation curve, shown for comparison in diagram 1, of laminated glass with the structure 4 mm of glass/0.76 mm of standard PVB/4 mm of glass, with 26% by weight of 3G7 as plasticizer, shows a clear drop in insulation between 1000 and 2000 Hz. This phenomenon is known as coincidence drop and represents a characteristic weakness ~~ with respect to sound exclusion - of laminated glass produced with standard
PVB.
The relative minimum in the sound insulation in the coincidence region is at about 1900 Hz, i.e. the coincidence frequency is 1900 Hz. At this frequency the insulation, at about 31.5 dB, 1s more than 5 dB below the corresponding value for the film according to example 1.
REPLACEMENT SHEET (RULE 26)
a - 10 -
Examples 3 to 7
The examples 3 to 7 given in the table below were carried out as for example 1. The sound insulation curves for these examples 3 to 7 were at a level similar to the curve according to example 1. mr Le [T constituent (comparative)
FER SE EE EN EN SE ser® lp le [2 | Jies| [- prurior® 00 luo [fa [0] [ artopne® we 120 | |= [in | [es] [ ariopne® we 6 | |- [- - [0 1 [un poryraresoe | | | | [ ln [ property || | [| [ [mm]
Baze)r [os] | loos] Jo.26l-0.16 (tH Di-n-hexyl adipate (2) Triethylene glycol bis-n-heptanoate (3) Poly(ethylene glycol) with an average molecular weight of 600 [g/mol] 4 Monolaterally substituted PEG with a polyethylene glycol fraction with a DP of 12 and an isononylphenol fraction on one of the two hydroxyl-terminated ends. © Bilaterally substituted PEG with a polyethylene glycol fraction with a DP of 6 and an : isononylphenol fraction on one of the two hydroxyl-terminated ends. (6) polybutylene glycol with a DP of about 9 from
BASF.
REPLACEMENT SHEET (RULE 26)
7 Sound insulation value in dB measured to
DIN EN ISO 717.
For all of the films of the examples the haze values found for the laminated glass were low and comparable with those for laminated glass laminated using a 2VE film plasticized in a manner known per se. Despite the increased total plasticizer content, 33% by weight compared with 26% by weight in comparative example 2, there was no significant impairment of the handling properties of the film, in particular its tack. In comparison with this, a film with 33% by weight of 3G7 content would have a limited capability for further processing using conventional systems, due to high tack - as a result of plasticizer exudation.
REPLACEMENT SHEET (RULE 26)
Claims (8)
1. Laminated safety glass, comprising - a first and a second pane of glass, and also, - arranged between the first and the second pane of glass, an intermediate layer, where the intermediate layer has a water content of from
0.15 to 0.8% by weight and comprises: - from 50 to 80% by weight of partially acetalized polyvinyl alcohol - from 20 to 50% by weight of a plasticizer mixture, comprising - from 30 to 70% by weight - calculated as proportion of the plasticizer mixture - of one or more polyalkylene glycols selected from the group consisting of - polyalkylene glycols of the general formula HO-(R-0O),—-H, where R = alkylene and n > 5, - block copolymers of ethylene glycol and propylene glycol having the general formula HO- (CH,—CH,-0) s— (CH,-CH (CH3) -0) o—H, where n > 2, m > 3, and (n+m) < 25, - derivatives of block copolymers of ethylene glycol and propylene glycol having the general formula R;0- (CH;-CH,-0) n—~ (CH,~CH (CH3) =O) n—H or HO- (CH,-CH,-0) n~ (CH,~-CH (CH3) =O) n—R1, where n> 2, m > 3, and (n+m) < 25 and R; as organic radical, - derivatives of polyalkylene glycols of the general formula R;-0-(R,-0)n—H, where R, = alkylene and n 2 2, in which the hydrogen of one of the two terminal hydroxyl groups of the polyalkylene glycol has been replaced by an organic radical Ri, - the proportion of the polyalkylene glycols AMENDED SHEET or 26-09-2001; of os0s won DE0002743 in the total mixture for the intermediate layer being greater than 5% by weight.
2. Laminated safety glass according to claim 1, characterized in that the polvalkylene glycols have been selected from the group consisting of - polyethylene glycol HO- (CH,-CH,-0)—H, where 8 <n < 25, - block copolymers of ethylene glycol and propylene glycol having the general formula HO- (CH,~CH,-0) n— (CH,-CH (CH3) =O) n—H, where n > 3, m > 4, and (n+m) < 20, - derivatives of block copolymers of ethylene glycol and propylene glycol having the general formula R,0- (CH,-CH2-0) ,— (CH2;—-CH (CH3) -O) n—H or HO- (CH,—CH»-0) n— (CH2,—-CH (CH3) =O) p—~R1, where n > 3, m > 4, and (n+m) < 20 and R; as organic radical, —- polybutylene glycol HO- (CH,—-CH;—-CH,-CH,-0) n-H, where 4 < n < 18, - derivatives of the polyethylene glycol of the general formula R;-O-(CH2-CH2-0),—H, where n 2 2 and R; 1s an organic radical, - derivatives of the polybutylene glycol of the general formula R;-O- (CH,—CH,-CH;—-CH,-0),—H, where n > 2 and R; is an organic radical.
3. Laminated safety glass according to claim 1 or 2, characterized in that the proportion of the polyalkylene glycols in the total mixture for the intermediate layer is greater than 10% by weight and less than 25% by weight.
4. Laminated safety glass according to any of claims 1 to 3, characterized in that at least one plasticizer selected from the group consisting of _ esters of polybasic aliphatic or aromatic acids, AMENDED SHEET
'. DE0002743 -polyhydric aliphatic or aromatic alcohols or oligoether glycols having not more than four ether units with one or more unbranched or branched aliphatic or aromatic substituents, is used as further plasticizer in the plasticizer mixture.
5. Laminated safety glass according to claim 4, characterized in that at least one of the plasticizer selected from the group consisting of dialkyl adipate, dialkyl sebacate, esters of di-, tri- or tetraglycols with linear or branched aliphatic carboxylic acids, is used as further plasticizer in the plasticizer mixture.
6. Laminated safety glass according to claim 4, characterized in that at least one plasticizer selected from the group consisting of di-n-hexyl adipate (DHA) and triethylene glycol bis—-n-heptanoate (3G7) is used as further plasticizer at a proportion > 10% by weight of the total mixture.
7. Laminated safety glass according to any of claims 1 to 6, characterized in that a polyvinyl butyral having from 19 to 22% by weight of vinyl alcohol radical and from 0.5 to 2.5% by weight of acetate radical is used as resin. AMENDED SHEET 13.09.2002
. DE0O002743
8. Sound-insulation film for producing laminated safety glass, comprising: - from 0.15 to 0.8% by weight of water, - from 50 to 80% by weight of partially acetalized polyvinyl alcohol, - from 20 to 50 by weight of a plasticizer mixture, comprising ~ from 30 to 70% by weight - calculated as proportion of the plasticizer mixture - of one or more polyalkylene glycols selected from the group consisting of - polyalkylene glycols of the general formula HO- (R-0)n, -H, where R = alkylene and n > 5, - block copolymers of ethylene glycol and propylene glycol having the general formula HO- (CH2-CH,-0), ~- (CH,-CH (CHjs) -0)p—H, where n > 2, m > 3, and (n+m) < 25, - derivatives of block copolymers of ethylene glycol and propylene glycol having the general formula R10- (CH2-CH,;-0) ,— {(CH2—CH (CH3) -0)p—H or HO- (CH2-CH2-0) ,- (CH=CH (CH3) -0)n~R;, where n > 2, m > 3, and (n+m) < 25 and R; as organic radical, - derivatives of polyalkylene glycols of the general formula R;,-0-(Ry;-0),-H, where R, = alkylene and n > 2, in which the hydrogen of one of the two terminal hydroxyl groups of the polyalkylene glycol has been replaced by an organicradical Rq, AMENDED SHEET 13.09.2002
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19938159A DE19938159A1 (en) | 1999-08-16 | 1999-08-16 | Acoustically insulating film, useful for the production of laminated safety glass, comprises partially acetalized polyvinyl alcohol containing a polyalkylene glycol or derivative |
Publications (1)
Publication Number | Publication Date |
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ZA200201393B true ZA200201393B (en) | 2003-04-30 |
Family
ID=7918122
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200201393A ZA200201393B (en) | 1999-08-16 | 2002-02-19 | Compound safety glass and PVB foil for the production thereof. |
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US (1) | US6887577B1 (en) |
EP (1) | EP1181258B1 (en) |
AT (1) | ATE220651T1 (en) |
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BR (1) | BR0013401B1 (en) |
CA (1) | CA2382141C (en) |
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ES (1) | ES2180521T3 (en) |
MX (1) | MXPA02001586A (en) |
RU (1) | RU2270099C2 (en) |
TW (1) | TWI254703B (en) |
WO (1) | WO2001019747A1 (en) |
ZA (1) | ZA200201393B (en) |
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1999
- 1999-08-16 DE DE19938159A patent/DE19938159A1/en not_active Withdrawn
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2000
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- 2000-08-16 WO PCT/DE2000/002743 patent/WO2001019747A1/en active IP Right Grant
- 2000-08-16 DE DE50000292T patent/DE50000292D1/en not_active Expired - Lifetime
- 2000-08-16 TW TW089116480A patent/TWI254703B/en not_active IP Right Cessation
- 2000-08-16 BR BRPI0013401-5A patent/BR0013401B1/en not_active IP Right Cessation
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- 2000-08-16 US US10/049,850 patent/US6887577B1/en not_active Expired - Fee Related
- 2000-08-16 CZ CZ20020560A patent/CZ297137B6/en not_active IP Right Cessation
- 2000-08-16 AT AT00965753T patent/ATE220651T1/en not_active IP Right Cessation
- 2000-08-16 DE DE10082758T patent/DE10082758D2/en not_active Expired - Fee Related
- 2000-08-16 EP EP00965753A patent/EP1181258B1/en not_active Expired - Lifetime
-
2002
- 2002-02-19 ZA ZA200201393A patent/ZA200201393B/en unknown
Also Published As
Publication number | Publication date |
---|---|
CA2382141C (en) | 2008-05-20 |
CZ297137B6 (en) | 2006-09-13 |
CA2382141A1 (en) | 2001-03-22 |
CZ2002560A3 (en) | 2003-12-17 |
DE10082758D2 (en) | 2002-08-14 |
EP1181258B1 (en) | 2002-07-17 |
MXPA02001586A (en) | 2002-07-02 |
WO2001019747A1 (en) | 2001-03-22 |
BR0013401B1 (en) | 2009-01-13 |
TWI254703B (en) | 2006-05-11 |
ES2180521T3 (en) | 2003-02-16 |
AU776416B2 (en) | 2004-09-09 |
ATE220651T1 (en) | 2002-08-15 |
US6887577B1 (en) | 2005-05-03 |
BR0013401A (en) | 2002-04-30 |
DE50000292D1 (en) | 2002-08-22 |
RU2270099C2 (en) | 2006-02-20 |
AU7641500A (en) | 2001-04-17 |
EP1181258A1 (en) | 2002-02-27 |
DE19938159A1 (en) | 2001-02-22 |
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